US20250270359A1 - Composition for forming resist underlayer film - Google Patents

Composition for forming resist underlayer film

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Publication number
US20250270359A1
US20250270359A1 US18/858,587 US202318858587A US2025270359A1 US 20250270359 A1 US20250270359 A1 US 20250270359A1 US 202318858587 A US202318858587 A US 202318858587A US 2025270359 A1 US2025270359 A1 US 2025270359A1
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group
underlayer film
resist underlayer
forming
polymer
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Daisuke Maruyama
Takafumi Endo
Takahiro Kishioka
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Nissan Chemical Corp
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Nissan Chemical Corp
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Assigned to NISSAN CHEMICAL CORPORATION reassignment NISSAN CHEMICAL CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MARUYAMA, DAISUKE, ENDO, TAKAFUMI, KISHIOKA, TAKAHIRO
Publication of US20250270359A1 publication Critical patent/US20250270359A1/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/094—Multilayer resist systems, e.g. planarising layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/20—Exposure; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor

Definitions

  • the present invention it is possible to provide a composition for forming a resist underlayer film, a resist underlayer film, a semiconductor processing substrate, a method for manufacturing a semiconductor element, and a pattern forming method capable of suppressing generation of fine particulate etching residues.
  • FIG. 1 A is a particle size distribution of a sample 1st of a polymer solution of Synthesis Example 1.
  • FIG. 2 B is a particle size distribution of a sample 2nd of the polymer solution of Synthesis Example 2.
  • a composition for forming a resist underlayer film of the present invention contains a polymer and a solvent.
  • Examples of the cause of the etching residues include metal impurities in the composition. However, as a result of examination by the present inventors, the fine particulate etching residues are not caused by metal impurities.
  • the polymer contained in the composition for forming a resist underlayer film affects the fine particulate etching residues. It was found that there was a part difficult to be etched in the polymer, and the part caused etching residues.
  • copolymerization reactivity ratios between the monomers are different, and thus copolymerization composition ratios of polymers generated in an early stage of polymerization and a late stage of polymerization are different, and a finally obtained polymer has a composition distribution.
  • the lactone structure-containing monomer has a higher polymerization rate in copolymerization than other monomers. Therefore, as described in Example (for example, Synthesis Examples 1 to 5) of WO2003/017002, when two or more types of monomers are mixed at once and polymerized according to the composition ratio in the finally obtained polymer, it is considered that a relatively large amount of the lactone structure-containing monomer is consumed in the initial stage of polymerization, and as a result, repeating units derived from the lactone structure-containing monomer are unevenly distributed in the polymer chain generated in the initial stage of polymerization. When the repeating unit derived from the lactone structure-containing monomer is unevenly distributed in the polymer chain, entanglement of the polymer chain increases. As a result, this is considered to decrease the solubility of the polymer and increase the average particle size of the polymer in the polymer solution.
  • the average particle size of the polymer in the polymer solution containing the polymer is 50 nm or less, preferably 40 nm or less, more preferably 30 nm or less, and particularly preferably 20 nm or less.
  • the lower limit of the average particle size of the polymer is not particularly limited, but may be 1 nm or more, 2 nm or more, or 5 nm or more.
  • the average particle size of the polymer in the polymer solution can be determined by dynamic light scattering measurement.
  • the dynamic light scattering measurement is performed using, for example, a dynamic light scattering photometer DLS-8000Ar (manufactured by Otsuka Electronics Co., Ltd.). Measurement is performed at a scattering angle of 90° using a He—Ne laser (optical wavelength: 633 nm) as incident light, and an autocorrelation function is obtained. With respect to the obtained autocorrelation function, the average particle size and the polydispersity index can be determined by cumulant analysis using an analysis program attached to the above measuring apparatus. Particle size distribution analysis can be performed by the Contin method.
  • the above polydispersity index of the present invention is, for example, 0.25 or less, 0.24 or less, 0.23 or less, 0.22 or less, 0.21 or less, 0.20 or less, 0.18 or less, or 0.15 or less.
  • the solvent in the polymer solution is preferably a solvent used for polymerization of the polymer. Therefore, a polymer solution obtained by polymerizing a monomer in a solvent is preferably used as it is as a polymer solution for measuring the average particle size.
  • the solvent used for polymerization of the polymer include polyhydric alcohol derivatives. Examples of the polyhydric alcohol derivatives include ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, and propylene glycol monomethyl ether acetate.
  • the concentration of the polymer in the polymer solution is preferably 10 to 30% by mass.
  • entanglement between polymer chains occurs to some extent in the polymer solution, and a result correlated with generation of fine particulate etching residues is more easily obtained.
  • the amount of the polymer in the composition for forming a resist underlayer film is small, even when an attempt is made to measure the average particle size of the polymer using the composition for forming a resist underlayer film, it is difficult to obtain a result correlated with the generation of fine particulate etching residues.
  • the reason for this is considered to be that when the concentration of the polymer is low, entanglement between polymer chains is less likely to occur.
  • the composition for forming a resist underlayer film as a product may also contain components other than the polymer (for example, a crosslinking agent, a curing catalyst, and other components), and when the dynamic light scattering measurement is performed on the composition for forming a resist underlayer film, the particle size distribution of the polymer and the particle size distribution of the components other than the polymer are mixed in the obtained particle size distribution, and it is difficult to obtain a result correlated with the generation of fine particulate etching residues.
  • components other than the polymer for example, a crosslinking agent, a curing catalyst, and other components
  • the average particle size when the average particle size is measured in the present invention, it is suitable to use a polymer solution, and it is more suitable to use a polymer solution having a polymer concentration of 10 to 30% by mass. Furthermore, it is suitable to use a polymer solution in which only a polymer is dissolved in a solvent without containing a crosslinking agent, a curing catalyst, or the like.
  • the polymer contains a repeating unit (1) represented by the following Formula (1).
  • the polymer also has a repeating unit (2) other than the repeating unit (1).
  • the polymer can be said to be a copolymer.
  • R 1 represents a hydrogen atom, a methyl group, or a halogen atom
  • R 2 represents a trivalent hydrocarbon group having 3 to 6 carbon atoms.
  • the lactone structure containing R 2 is a 5-membered ring or a 6-membered ring.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Examples of the repeating unit (1) represented by Formula (1) include repeating units represented by the following Formulas (1-1) to (1-3).
  • R 1 represents a hydrogen atom, a methyl group, or a halogen atom.
  • R 1 in Formula (1) and Formulas (1-1) to (1-3) is preferably a methyl group.
  • the repeating unit (2) is not particularly limited as long as the repeating unit (2) is a repeating unit other than the repeating unit (1) represented by Formula (1), but the repeating unit (2) preferably includes a repeating unit (2A) represented by the following Formula (2A).
  • R 11 represents a hydrogen atom, a methyl group, or a halogen atom
  • Q 1 represents a single bond or a divalent linking group
  • R 12 represents a hydrogen atom or a monovalent organic group.
  • the divalent linking group in Q 1 is not particularly limited, and examples thereof include —C( ⁇ O)O—, —O—, —C( ⁇ O)—N(—R)— (R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), —NHC( ⁇ O)NH— (urea bond), —NHC( ⁇ O)O— (urethane bond), —C( ⁇ O)—, —S—, —SO—, and —NH—.
  • Examples of the monovalent organic group in R 12 include a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted carbocyclic aromatic group, and a substituted or unsubstituted heterocyclic aromatic group.
  • substituents include a halogen atom, a hydroxy group, a carboxy group, an alkoxy group, a cyano group, a nitro group, and an amino group.
  • alkoxy group include an alkoxy group having 1 to 6 carbon atoms.
  • the “1 to 10 carbon atoms” in the “substituted or unsubstituted alkyl group having 1 to 10 carbon atoms” does not include the number of carbon atoms of the substituent.
  • Examples of the aralkyl group in the substituted or unsubstituted aralkyl group include a benzyl group, a phenethyl group, a naphthylmethyl group, and an anthrylmethyl group.
  • Examples of the carbocyclic aromatic group in the substituted or unsubstituted carbocyclic aromatic group include a phenyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
  • Examples of the substituted or unsubstituted carbocyclic aromatic group include a phenyl group, an o-methylphenyl group, an m-methylphenyl group, a p-methylphenyl group, an o-chlorophenyl group, an m-chlorophenyl group, a p-chlorophenyl group, an o-fluorophenyl group, a p-fluorophenyl group, an o-methoxyphenyl group, a p-methoxyphenyl group, a p-nitrophenyl group, a p-cyanophenyl group, an a-naphthyl group, a B-naphthyl group, an o-biphenylyl group, an m-biphenylyl group, a p-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl
  • heterocyclic aromatic group in the substituted or unsubstituted heterocyclic aromatic group examples include a pyridyl group, a quinolinyl group, and a quinoxalinyl group.
  • the repeating unit (2) preferably includes a repeating unit (2A-1) represented by the following Formula (2A-1) and a repeating unit (2A-2) represented by the following Formula (2A-2).
  • X 21 represents —O— or —N(—R)— (R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
  • R 21 represents a hydrogen atom, a methyl group, or a halogen atom, and
  • R 22 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
  • X 31 represents —O— or —N(—R)— (R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
  • R 3 represents a hydrogen atom, a methyl group, or a halogen atom, and
  • R 32 represents a substituted or unsubstituted aralkyl group, a substituted or unsubstituted carbocyclic aromatic group, or a substituted or unsubstituted heterocyclic aromatic group.
  • R 22 Specific examples of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms in R 22 include specific examples of the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms in the description of R 12 .
  • substituted or unsubstituted aralkyl group, the substituted or unsubstituted carbocyclic aromatic group, and the substituted or unsubstituted heterocyclic aromatic group in R 32 include specific examples of the substituted or unsubstituted aralkyl group, the substituted or unsubstituted carbocyclic aromatic group, and the substituted or unsubstituted heterocyclic aromatic group in the description of R 12 .
  • R 11 in Formula (2A), R 21 in Formula (2A-1), and R 31 in Formula (2A-2), a methyl group is preferred.
  • the proportion of the repeating unit (1) in the polymer is not particularly limited.
  • the weight ratio of the repeating unit (1) to all repeating units in the polymer is preferably 1 to 75% by weight, more preferably 5 to 60% by weight, and particularly preferably 10 to 45% by weight.
  • the weight ratio of the repeating unit (2) to all repeating units in the polymer is not particularly limited, but is preferably 25 to 99% by weight, more preferably 40 to 95% by weight, and particularly preferably 55 to 90% by weight.
  • the total weight ratio of the repeating unit (2A-1) and the repeating unit (2A-2) to all repeating units in the polymer is not particularly limited, but is preferably 25 to 99% by weight, more preferably 40 to 95% by weight, and particularly preferably 55 to 90% by weight.
  • the molecular weight of the polymer is not particularly limited.
  • the weight average molecular weight of the polymer measured by gel permeation chromatography is not particularly limited, but is preferably 100,000 or less, more preferably 50,000 or less, and particularly preferably 30,000 or less.
  • the lower limit of the weight average molecular weight of the polymer is not particularly limited, but the weight average molecular weight is preferably 5,000 or more.
  • the polymer is obtained by radical polymerization of two or more types of monomers.
  • One of the two or more types of monomers is a monomer represented by the following Formula (1′).
  • the method for manufacturing a polymer is a manufacturing method in which the average particle size of a polymer in a polymer solution is reduced.
  • Examples of such a manufacturing method include a method for manufacturing a polymer described in WO2012/053434. Specific examples thereof include polymerization methods (Z1) and (Z2) described in [0062] to [0066] of WO2012/053434. The contents of WO2012/053434 are incorporated herein to the same extent as all specified.
  • the method for manufacturing a polymer include the methods for manufacturing a polymer described in Reference Example B-3 and Example B-3 of WO2012/053434.
  • the monomer represented by the following Formula (1′) in the present specification corresponds to the monomer m-1 represented by Formula (m-1) in Reference Example B-3 of WO2012/053434 A.
  • the monomer represented by the following Formula (2A′-1) in the present specification corresponds to the monomer m-7 represented by Formula (m-7) in Reference Example B-3 of WO2012/053434.
  • the monomer represented by the following Formula (2A′-2) in the present specification corresponds to the monomer m-6 represented by Formula (m-6) in Reference Example B-3 of WO2012/053434.
  • a dropping solution containing a monomer mixture, a solvent, and a polymerization initiator is added dropwise into the flask from a dropping funnel at a constant dropping rate over 4 hours, and a temperature of 80° C. is further maintained for 3 hours. Then, after 7 hours from the start of dropwise addition of the dropping solution, the reaction is stopped by cooling to room temperature.
  • Example B-3 Based on the result of Reference Example B-3, in Example B-3, after the main step of supplying Sa into the reactor in advance and adding Tb and the polymerization initiator solution dropwise, a post-step of dropping Uc is provided.
  • the composition ratio of the monomer m-1 having a high polymerization rate is smaller than the composition ratio of the monomer m-1 in the target composition.
  • the monomer that gives the repeating unit (1) represented by Formula (1) to the polymer is a monomer represented by the following Formula (1′).
  • R 1 and R 2 have the same meanings as R 1 and R 2 in Formula (1), respectively.
  • the monomer that gives the repeating unit represented by Formula (1-1) to the polymer is a monomer represented by the following Formula (1′-1).
  • the monomer that gives the repeating unit represented by Formula (1-2) to the polymer is a monomer represented by the following Formula (1′-2).
  • the monomer that gives the repeating unit represented by Formula (1-3) to the polymer is a monomer represented by the following Formula (1′-3).
  • R 1 has the same meaning as R 1 in Formula (1-2).
  • the monomer that gives the repeating unit (2A) represented by Formula (2A) to the polymer is a monomer represented by the following Formula (2A′).
  • diacyl peroxides examples include diacetyl peroxide, diisobutyl peroxide, didecanoyl peroxide, benzoyl peroxide, and succinic acid peroxide.
  • R 1 represents a methyl group or an ethyl group. * represents a bonding site bonded to a nitrogen atom.
  • the nitrogen-containing compound having 2 to 6 substituents represented by the Formula (1d) in one molecule is obtained by reacting a nitrogen-containing compound having 2 to 6 substituents, which are represented by the following Formula (2d) and bonded to a nitrogen atom, in one molecule with at least one compound represented by the following Formula (3d).
  • R 2 and R 3 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and R 4 each independently represents an alkyl group having 1 to 4 carbon atoms.
  • glycoluril derivative represented by the Formula (2E) examples include compounds represented by the following Formulas (2E-1) to (2E-4). Furthermore, examples of the compound represented by the Formula (3d) include compounds represented by the following Formulas (3d-1) and (3d-2).
  • the above crosslinking agent may be a crosslinkable compound represented by the following Formula (G-1) or (G-2) described in WO2014/208542.
  • Q 1 represents a single bond or an m1-valent organic group
  • R 1 and R 4 each represent an alkyl group having 2 to 10 carbon atoms or an alkyl group having 2 to 10 carbon atoms having an alkoxy group having 1 to 10 carbon atoms
  • R 2 and R 5 each represent a hydrogen atom or a methyl group
  • R 3 and R 6 each represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 40 carbon atoms.
  • n1 represents an integer of 1 ⁇ n1 ⁇ 3
  • n2 represents an integer of 2 ⁇ n2 ⁇ 5
  • n3 represents an integer of 0 ⁇ n3 ⁇ 3
  • n4 represents an integer of 0 ⁇ n4 ⁇ 3, with an integer of 3 ⁇ (n1+n2+n3+n4) 6.
  • n5 represents an integer of 1 ⁇ n5 ⁇ 3
  • n6 represents an integer of 1 ⁇ n6 ⁇ 4
  • n7 represents an integer of 0 ⁇ n7 ⁇ 3
  • n8 represents an integer of 0 ⁇ n8 ⁇ 3, with an integer of 2 ⁇ (n5+n6+n7+n8) ⁇ 5.
  • n 1 to 10.
  • the crosslinkable compound represented by above-described Formula (G-1) or (G-2) may be obtained by reaction of a compound represented by the following Formula (G-3) or (G-4) with a hydroxyl group-containing ether compound or an alcohol having 2 to 10 carbon atoms.
  • Q 2 represents a single bond or an m2-valent organic group.
  • R 8 , R 9 , R 11 , and R 12 each represent a hydrogen atom or a methyl group
  • R 7 and R 10 each represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 40 carbon atoms.
  • n9 represents an integer of 1 ⁇ n9 ⁇ 3
  • n10 represents an integer of 2 ⁇ n10 ⁇ 5
  • n11 represents an integer of 0 ⁇ n11 ⁇ 3
  • n12 represents an integer of 0 ⁇ n12 ⁇ 3, with an integer of 3 ⁇ (n9+n10+n11+n12) ⁇ 6.
  • n13 represents an integer of 1 ⁇ n13 ⁇ 3
  • n14 represents an integer of 1 ⁇ n14 ⁇ 4
  • n15 represents an integer of 0 ⁇ n15 ⁇ 3
  • n16 represents an integer of 0 ⁇ n16 ⁇ 3, with an integer of 2 ⁇ (n13+n14+n15+n16) ⁇ 5.
  • n2 represents an integer of 2 to 10.
  • Me represents a methyl group.
  • the content ratio of the crosslinking agent in the composition for forming a resist underlayer film is, for example, 1% by mass to 50% by mass, and preferably 5% by mass to 40% by mass with respect to the polymer.
  • both a thermal acid generator and a photoacid generator can be used, but it is preferable to use a thermal acid generator.
  • thermal acid generator examples include sulfonic acid compounds and carboxylic acid compounds such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate (pyridinium-p-toluenesulfonic acid), pyridinium phenol sulfonic acid, pyridinium-p-hydroxybenzenesulfonic acid (p-phenolsulfonic acid pyridinium salt), pyridinium-trifluoromethanesulfonic acid, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid, 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, and hydroxybenzoic acid.
  • carboxylic acid compounds such as p-toluenesulf
  • Examples of the photoacid generator include an onium salt compound, a sulfonimide compound, and a disulfonyl diazomethane compound.
  • onium salt compound examples include iodonium salt compounds such as diphenyliodonium hexafluorophosphate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoronormalbutanesulfonate, diphenyliodonium perfluoronormaloctanesulfonate, diphenyliodonium camphorsulfonate, bis(4-tert-butylphenyl)iodonium camphorsulfonate, and bis(4-tert-butylphenyl)iodonium trifluoromethanesulfonate; and sulfonium salt compounds such as triphenylsulfonium hexafluoroantimonate, triphenylsulfonium nonafluoronormalbutanesulfonate, triphenylsulfonium camphorsulfonate, and triphenylsulfonium triflu
  • sulfonimide compound examples include N-(trifluoromethanesulfonyloxy) succinimide, N-(nonafluoronormalbutanesulfonyloxy)succinimide, N-(camphorsulfonyloxy)succinimide, and N-(trifluoromethanesulfonyloxy)naphthalimide.
  • disulfonyl diazomethane compound examples include bis(trifluoromethylsulfonyl)diazomethane, bis(cyclohexylsulfonyl)diazomethane, bis(phenylsulfonyl)diazomethane, bis(p-toluenesulfonyl)diazomethane, bis(2,4-dimethylbenzenesulfonyl)diazomethane, and methylsulfonyl-p-toluenesulfonyl diazomethane.
  • the content ratio of the curing catalyst is, for example, 0.1% by mass to 50% by mass, and preferably 1% by mass to 30% by mass with respect to the crosslinking agent.
  • an organic solvent generally used for a chemical solution for a semiconductor lithography process is preferable.
  • examples thereof include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, cycloheptanone, 4-methyl-2 pentanol, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, ethyl ethoxyacetate, 2-hydroxy
  • propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, and cyclohexanone are preferable.
  • propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate are preferable.
  • a surfactant can be further added in order to further improve the coating property for surface unevenness without generating pinholes, striations, and the like.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ethers (for example, polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene oleyl ether), polyoxyethylene alkyl allyl ethers (for example, polyoxyethylene octylphenol ether and polyoxyethylene nonylphenol ether), polyoxyethylene/polyoxypropylene block copolymers, sorbitan fatty acid esters (for example, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan tristearate), polyoxyethylene sorbitan fatty acid esters (for example, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, and polyoxyethylene
  • the blending amount of these surfactants is not particularly limited, but is usually 2.0% by mass or less, and preferably 1.0% by mass or less with respect to the total solid content of the composition for forming a resist underlayer film.
  • surfactants may be added alone, or may be added in combination of two or more thereof.
  • the film forming component contained in the composition for forming a resist underlayer film that is, the component excluding the solvent is, for example, 0.01% by mass to 10% by mass of the composition for forming a resist underlayer film.
  • the resist underlayer film of the present invention is a cured product of the composition for forming a resist underlayer film described above.
  • the resist underlayer film can be manufactured, for example, by coating a semiconductor substrate with the above-described composition for forming a resist underlayer film and baking the composition.
  • Examples of the semiconductor substrate coated with the composition for forming a resist underlayer film include silicon wafers, germanium wafers, and compound semiconductor wafers such as gallium arsenide, indium phosphide, gallium nitride, indium nitride, and aluminum nitride.
  • the inorganic film is formed by, for example, an atomic layer deposition (ALD) method, a chemical vapor deposition (CVD) method, a reactive sputtering method, an ion plating method, a vacuum deposition method, or a spin coating method (spin on glass: SOG).
  • ALD atomic layer deposition
  • CVD chemical vapor deposition
  • SOG spin coating method
  • the inorganic film examples include a polysilicon film, a silicon oxide film, a silicon nitride film, a boro-phospho silicate glass (BPSG) film, a titanium nitride film, a titanium nitride oxide film, a tungsten film, a gallium nitride film, and a gallium arsenide film.
  • the inorganic film may be a single layer or a multilayer of two or more layers. In the case of multiple layers or more, each layer may be the same type of inorganic film or different types of inorganic films.
  • the thickness of the inorganic film is not particularly limited.
  • the lower limit of the film thickness of the resist underlayer film is, for example, 1 nm, 2 nm, 3 nm, 5 nm, 10 nm, 20 nm, 30 nm, 40 nm, 50 nm, 70 nm, 80 nm, 90 nm, or 100 nm
  • the upper limit is, for example, 10 ⁇ m, 8 ⁇ m, 5 ⁇ m, 3 ⁇ m, 2 ⁇ m, 1 ⁇ m, 900 nm, 800 nm, 700 nm, 600 nm, 500 nm, 400 nm, 300 nm, or 200 nm.
  • the method of measuring the film thickness of the resist underlayer film in the present specification is as follows.
  • the resist underlayer film is disposed, for example, on a semiconductor substrate.
  • the pattern forming method of the present invention includes at least the following steps:
  • the film thickness of the resist film is preferably 200 nm or less, more preferably 150 nm or less, still more preferably 100 nm or less, and particularly preferably 80 nm or less. Further, the film thickness of the resist film is preferably 10 nm or more, more preferably 20 nm or more, and particularly preferably 30 nm or more.
  • the resist formed on the resist underlayer film for example, by coating and baking by a known method is not particularly limited as long as the resist responds to the light or electron beam (EB) used for irradiation. Both a negative photoresist and a positive photoresist can be used.
  • EB electron beam
  • a resist responding to EB is also referred to as a photoresist.
  • the photoresist examples include a positive photoresist composed of a novolak resin and 1,2-naphthoquinone diazide sulfonic acid ester; a chemically amplified photoresist composed of a photoacid generator and a binder having a group which is decomposed by an acid to increase the alkali dissolution rate; a chemically amplified photoresist composed of a low molecular compound which is decomposed by an acid to increase the alkali dissolution rate of the photoresist, an alkali-soluble binder, and a photoacid generator; a chemically amplified photoresist composed of a binder that has a group which is decomposed by an acid to increase the alkali dissolution rate, a low molecular compound which is decomposed by an acid to increase the alkali dissolution rate of the photoresist, and a photoacid generator; and a resist containing metal elements.
  • Examples thereof include product name V146G manufactured by JSR Corporation, product name APEX-E manufactured by Shipley, product name PAR710 manufactured by Sumitomo Chemical Co., Ltd., and product names AR2772 and SEPR430 manufactured by Shin-Etsu Chemical Co., Ltd. Further, examples thereof include a fluorine-containing atomic polymer-based photoresist as described in Proc. SPIE, Vol. 3999, 330-334 (2000), Proc. SPIE, Vol. 3999, 357-364 (2000), or Proc. SPIE, Vol. 3999, 365-374 (2000).
  • Examples of the resist composition include the following compositions.
  • n represents an integer of 1 to 6.
  • R 1 and R 2 each independently represent a fluorine atom or a perfluoroalkyl group.
  • L 1 represents —O—, —S—, —COO—, —SO 2 —, or —SO 3 —.
  • L 2 represents an alkylene group optionally having a substituent or a single bond.
  • W 1 represents a cyclic organic group which may have a substituent.
  • a metal-containing film forming composition for extreme ultraviolet ray or electron beam lithography containing: a compound having a metal-oxygen covalent bond; and a solvent, in which metal elements constituting the above compound belong to the third to seventh periods of Groups 3 to 15 of the periodic table.
  • Ar is a group obtained by removing (n+1) hydrogen atoms from an arene having 6 to 20 carbon atoms.
  • R 1 is a hydroxy group, a sulfanyl group, or a monovalent organic group having 1 to 20 carbon atoms.
  • n is an integer of 0 to 11. When n is 2 or more, a plurality of R 1 are the same or different.
  • R 2 is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
  • R 3 is a monovalent group having 1 to 20 carbon atoms and containing the above acid-dissociable group.
  • Z is a single bond, an oxygen atom or a sulfur atom.
  • R 4 is a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
  • a resist composition containing: a resin (A1) containing a structural unit having a cyclic carbonate structure, a structural unit represented by the following formula, and a structural unit having an acid-unstable group; and an acid generator.
  • R A are each independently a hydrogen atom or a methyl group.
  • R 1 and R 2 are each independently a tertiary alkyl group having 4 to 6 carbon atoms.
  • R 3 is each independently a fluorine atom or a methyl group.
  • m is an integer of 0 to 4.
  • X 1 is a single bond, a phenylene group or a naphthylene group, or a linking group having 1 to 12 carbon atoms containing at least one selected from an ester bond, a lactone ring, a phenylene group, and a naphthylene group.
  • X 2 is a single bond, an ester bond, or an amide bond.
  • Examples of the resist material include the following.
  • R A is a hydrogen atom or a methyl group.
  • X 1 is a single bond or an ester group.
  • X 2 is a linear, branched, or cyclic alkylene group having 1 to 12 carbon atoms or an arylene group having 6 to 10 carbon atoms, and a part of the methylene group constituting the alkylene group may be substituted with an ether group, an ester group, or a lactone ring-containing group, and at least one hydrogen atom contained in X 2 is substituted with a bromine atom.
  • X 3 is a single bond, an ether group, an ester group, or a linear, branched, or cyclic alkylene group having 1 to 12 carbon atoms, and a part of the methylene group constituting the alkylene group may be substituted with an ether group or an ester group.
  • Rf 1 to Rf 4 are each independently a hydrogen atom, a fluorine atom, or a trifluoromethyl group, and at least one of Rf 1 to Rf 4 is a fluorine atom or a trifluoromethyl group.
  • Rf 1 and Rf 2 may be combined to form a carbonyl group.
  • R 1 to R 5 are each independently a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, a linear, branched, or cyclic alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or an aryloxyalkyl group having 7 to 12 carbon atoms, some or all of hydrogen atoms of these groups may be substituted with a hydroxy group, a carboxy group, a halogen atom, an oxo group, a cyano group, an amide group, a nitro group, a sultone group, a sulfone group, or a sulfonium salt-containing group, and some of methylene groups constituting these groups may be substituted with an ether group, an ester group, a carbonyl group, a carbonate group
  • R A is a hydrogen atom or a methyl group.
  • R 1 is a hydrogen atom or an acid-unstable group.
  • R 2 is a linear, branched, or cyclic alkyl group having 1 to 6 carbon atoms or a halogen atom other than bromine.
  • X 1 is a single bond or a phenylene group, or a linear, branched, or cyclic alkylene group having 1 to 12 carbon atoms which may contain an ester group or a lactone ring.
  • X 2 is —O—, —O—CH 2 —, or —NH—.
  • m is an integer of 1 to 4.
  • u is an integer of 0 to 3.
  • m+u is an integer of 1 to 4.
  • a resist composition which generates an acid by exposure and of which solubility in a developer is changed by an action of the acid the resist composition containing:
  • Rf 21 are each independently a hydrogen atom, an alkyl group, an alkoxy group, a hydroxyl group, a hydroxyalkyl group, or a cyano group.
  • n is an integer of 0 to 2. * is a bonding site.
  • the constituent unit (f1) includes a constituent unit represented by the following general Formula (f1-1) or a constituent unit represented by the following general Formula (f1-2).
  • R are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms.
  • X is a divalent linking group having no acid-dissociable site.
  • a ary i is a divalent aromatic cyclic group which may have a substituent.
  • X 01 is a single bond or a divalent linking group.
  • R 2 are each independently an organic group having a fluorine atom.
  • Examples of the coating, the coating solution, and the coating composition include the following.
  • An inorganic oxo-hydroxo-based composition An inorganic oxo-hydroxo-based composition.
  • JP 11-135476 A proposes a technique of etching an organic antireflection film using a mixed gas of an O 2 (oxygen) gas and a halogen-based gas.
  • the semiconductor device can be manufactured through a step of processing the semiconductor substrate by a known method (dry etching method or the like).
  • the weight average molecular weight of the polymer shown in the following Synthesis Examples of the present specification is a measurement result by gel permeation chromatography (hereinafter abbreviated as GPC).
  • GPC gel permeation chromatography
  • a GPC apparatus manufactured by Tosoh Corporation was used, and measurement conditions and the like are as follows.
  • composition ratio of the obtained polymer is the composition ratio of the obtained polymer.
  • the obtained polymer had a weight average molecular weight of 89,000 and a number average molecular weight of 30,000.
  • polymerization was performed with reference to Reference Example B-3 and Example B-3 of WO2012/053434 to obtain a polymer solution having a solid content of 20% by mass.
  • composition ratio of the obtained polymer is the composition ratio of the obtained polymer.
  • the obtained polymer solution had a weight average molecular weight of 10,500 and a number average molecular weight of 5,300.
  • the dynamic light scattering measurement was performed using a dynamic light scattering photometer DLS-8000Ar (manufactured by Otsuka Electronics Co., Ltd.). Measurement was performed at a scattering angle of 90° using a He—Ne laser (optical wavelength: 633 nm) as incident light, and an autocorrelation function was obtained. With respect to the obtained autocorrelation function, the average particle size and the polydispersity index was determined by cumulant analysis using an analysis program attached to the above measuring apparatus. Particle size distribution analysis was performed by the Contin method. The results are shown in Table 1.
  • FIGS. 1 A to 1 C and FIGS. 2 A to 2 C represents a scattering intensity distribution.
  • the vertical axis (second axis) on the right side represents the integrated value of the scattering intensity distribution.

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